Hydrochloric Acid → 2-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-yl)-propanoic acid

HRID 900375Notes

Reaction equation

HRID 900375 reaction equation
C[O:2][C:3](=[O:39])[CH:4]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]4[O:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[C:22]=4[CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[K+].Cl>C1COCC1.CO.C(OCC)(=O)C>[C:35]([O:34][C:32]([NH:31][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]4[O:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[C:22]=4[CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[C:3]([OH:39])=[O:2])=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1317268262-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-yl)-propanoic acid methyl ester

Product 1

HCID 1317268272-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-yl)-propanoic acidYield 67%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-yl)-propanoic acid methyl ester (125 mg, 0.24 mmol) in THF (2 mL) and methanol (2 mL) was cooled to 0° C. and treated with 2 N KOH (1.0 mL). After stirring at room temperature for 1 h the solution was acidified with 10% HCl to pH 2 and diluted with ethyl acetate (25 mL). After being seperated, the aqueous layer was extracted with ethyl acetate (3×15 mL) and the combined organic layers were dried over MgSO4 and concentrated. Purification by flash column chromatography (2-5% methanol in dichloromethane) provided 2-tert-Butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-yl)-propanoic acid (80 mg, 67%) as white solid. 1H NMR (CDCl3), 7.98 (d, J=9 Hz, 2H), 7.93 (d, J=8 Hz, 2H), 7.74 (d, J=9, 2H), 7.59 (m, 4H), 7.41 (m, 5H), 5.01 (d, J=8 Hz, 1H), 4.66 (m, 1H), 3.30 (m, 2H), 1.47 (s, 9H). LCMS 408 (M+−100).

Workup

  1. customAfter being seperated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×15 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (2-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-70e1a26832ba4e8bbec473a2a70a9efd
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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